Great OP!
I was just about to start one, but this is a great one to say what I have to say about Pride Month.
1) There is nothing to be proud of in being homosexual, just like I have no reason to be proud of being heterosexual. I did nothing to earn being hetero, and you did nothing to earn being homo. We are what we are. If it were Acceptance Month, it would make more sense.
2) There is certainly nothing to be proud of in being trans. If you just like to play dress up as the opposite sex, and that's fun for you, it isn't a mental illness. It's just being weird and goofy. If you take it beyond that and are truly deluded that you really are the opposite sex and it makes you unhappy to be "in the wrong body," you do have a mental illness. It is recognized in the DSM-V as Gender Dysphoria. I hope you get help for that, and I would hope it would be help accepting your body, not help mutilating it. Whichever one you choose as an adult, mental illness is nothing to take pride in.
3) Recently LGBT-Q-W "Pride" took a much more ugly turn than people dressing up and parading. Now your movement is demanding the right to target children for grooming and mutilation and to target girl and women athletes for destruction of their sports category.
Damned if I'll buy a thin crust pepperoni, or a whoper from a company that will put it in a rainbow box this month.